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Silicone monomer

a technology of silicon monomer and silicon monomer, which is applied in the field of silicon monomer, can solve the problems of inconvenient use as soft contact lens material, inability to provide transparent monomers, and inability to use as lens materials, and achieve the effect of easy manufacturing and high purity

Active Publication Date: 2011-11-17
NOF CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

[0020]The silicone monomer of the present invention, which is easy to manufacture, may be obtained easily in high purity, and provides a colorless, transparent polymer when copolymerized with a polymerizable monomer such as a (meth)acrylic monomer, even when it is in a hydrous state. Thus the silicone monomer of the present invention may be used as a high purity ophthalmic monomer which is suitable for the art of ophthalmic devices wherein little isomers and by-products are desired, and is optimal as a contact lens material.

Problems solved by technology

However, TRIS is inferior in compatibility with hydrophilic monomers, such as 2-hydroxyethyl methacrylate (HEMA), and when copolymerized with such hydrophilic monomers, will not provide transparent monomers, and cannot be used as a lens material.
It is also known that combination of TRIS with other hydrophilic monomers often results in strongly water-repellent surfaces in a hydrous state, and thus inconvenient for use as a soft contact lens material (Non-patent Publication 1).
However, reaction of carboxylic acid and an epoxy group produces isomers (Non-patent Publication 2 and Patent Publication 4), which have similar properties, and are hard to be separated and purified for use through ordinary methods.
It is also known that, after formation of SiGMA, carboxylic acid is further added to the hydroxyl group in the glycerin portion of SiGMA to form by-products, which may adversely affect lens properties.
Thus it has been hard to produce hydrophilic monomer structures in an industrial scale by the reaction of a methacrylic halide and straight chain polyether-modified silicone.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

example 1

Synthesis of MASS (methacryloyloxyethyl succinate 3-[tris(trimethylsiloxy)silyl]propyl)

[0055]A 1 L pear-shaped flask was charged with 59.39 g of 2-methacryloyloxyethyl succinate (0.258 moles, manufactured by KYOEISHA CHEMICAL CO., LTD.), 637.56 g of N,N-dimethylformamide, 29.74 g potassium carbonate (0.215 moles), and 4-methoxyphenol, and the resulting solution was heated to 40° C. After the temperature was raised, 100.0 g of 3-iodopropyltris(trimethylsiloxy)silane (0.215 moles) was added dropwise, and the mixture was further stirred for 2 hours. The reaction solution was cooled, and then transferred to a 5 L separating funnel, diluted with 1200 g of ethyl acetate, washed three times with 1200 g of 5% sodium hydrogen carbonate, and further washed twice with 1200 g of 2% sodium sulfate. By removing the solvent, 112.9 g of a colorless, transparent silicone compound of the formula below was obtained (at 75.5% yield).

[0056]The purity of the obtained silicone compound was 91.1 mass %. Th...

example 2

Synthesis of AESS (acryloyloxyethyl succinate 3-[tris(trimethylsiloxy)silyl]propyl)

[0062]A 1 L pear-shaped flask was charged with 83.66 g of 2-acryloyloxyethyl succinate (0.387 moles, manufactured by KYOEISHA CHEMICAL CO., LTD.), 1018.32 g of N,N-dimethylformamide, 44.61 g of potassium carbonate (0.323 moles), and 4-methoxyphenol, and the resulting solution was heated to 40° C. After the temperature was raised, 150.0 g of 3-iodopropyltris(trimethylsiloxy)silane (0.323 moles) was added dropwise, and the mixture was further stirred for 2 hours. The reaction solution was cooled, and then transferred to a 5 L separating funnel, diluted with 1200 g of ethyl acetate, washed three times with 1200 g of 5% sodium hydrogen carbonate, and further washed twice with 2% sodium sulfate. By removing the solvent, 134.0 g of a colorless, transparent silicone compound of the formula below was obtained (at 75.0% yield).

[0063]By the 1H-NMR measurement of the obtained silicone compound, peaks derived fro...

example 3

Test on Contact Lens Model Containing Compound of Formula (2) Prepared in Example 1 as Polymerizable Component

[0067]40 parts by mass of the compound of formula (2) prepared in Example 1, 60 parts by mass of 2-hydroxyethylmethacrylate, 0.5 parts by mass of ethylene glycol dimethacrylate, and 0.5 parts by mass of azobisisobutyronitrile were mixed and dissolved. The resulting solution was poured into a cell made of a glass plate and a polypropylene plate with a 0.1 mm thick polyethylene terephthalate sheet interposed therebetween as a spacer. The atmosphere in an oven was substituted with nitrogen, and the cell was heated at 100° C. for 2 hours for polymerization. After polymerization, the cured sheet was taken out of the mold, soaked in a 3 / 1 mixed solution of ethyl alcohol and ion exchanged water for 12 hours, and then in ion exchanged water for 12 hours to obtain a hydrous film. The hydrous film thus obtained was prepared into the shapes required for various measurements, and the tr...

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Abstract

The invention provides a silicone monomer having high purity and suitable for use in the manufacture of ophthalmic devices, and a contact lens produced from the silicone monomer as a polymerizable component. The silicone monomer is represented by the formula (1):wherein Y1 to Y9 each independently stands for an alkyl group having 1 to 4 carbon atoms, n is an integer of 0 to 3, a and b each independently denotes an integer of 0 or 1, and R stands for a hydrogen atom or a methyl group.

Description

FIELD OF ART[0001]The present invention relates to silicone monomers for use in manufacture of ophthalmic devices, such as contact lenses, intraocular lenses, and keratoprosthesis. The silicone monomers of the present invention provide polymers of high transparency and oxygen permeability and suitable for application in the eyes, so that they are particularly suitable as monomers for contact lenses.BACKGROUND ART[0002]Silicone compounds such as TRIS and SiGMA represented by the formulae below are conventionally known as device monomers for contact lenses.[0003]TRIS stands for 3-[tris(trimethylsiloxy)silyl]propyl methacrylate, which is a monomer classically known as a material for intraocular lenses (Patent Publication 1). However, TRIS is inferior in compatibility with hydrophilic monomers, such as 2-hydroxyethyl methacrylate (HEMA), and when copolymerized with such hydrophilic monomers, will not provide transparent monomers, and cannot be used as a lens material.[0004]It is also kn...

Claims

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Application Information

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IPC IPC(8): C08L43/04C07F7/02C07F7/18
CPCA61F2/142A61F2/16C07F7/0852C08F220/28C08F222/1006C08F230/08G02B1/043G02C7/04C08L83/04C08L33/10C08L51/085C07F7/0838C08F222/102C08F220/20
Inventor MATSUOKA, YOSUKEYOSHIOKA, NOBUYUKISAKAMOTO, NOBUYUKIITEI, TOSHIYAKOBAYASHI, RYOTASORIMACHI, MAO
Owner NOF CORP